Hey I think a lot of us have been in your shoes before.
When I was 19 I was. I bought a Catalina 13 Cyclone. It's a 13' sailboat with just a mainsail. I trailered it everywhere, and it was fun, but I GOT BORED QUICK. Adding a little jib
on these day sailors doesn't really complicate things, you're going to have to (and want to) learn it eventually if you stick with sailing, and when you start to feel bored, it becomes another sail and sheet to trim and pay attention too, which is nice.
Trust me, you'll get envy of guys with jibs
and a place to sit and relax like on a Lido (14' or Catalina 14.2 or a Coronado 15. (And those have trapeze lines
which could be fun for a crew)
Buy something that mimics larger sailboats by the way it's controlled - trust me that's what you want. You want a jib
, traveler, boom vang, tiller extension, downhauls, outhauls, side stays, and a small space for storage (backpack, cooler, warm clothes). All of these things are a part of sailing any larger boat, so don't stop yourself short with a single sail and too simple of a boat. I did, and I had buyers remorse for over a year even though I loved sailing on it. But I kept looking at boats 14'-19' and wanting that. I wanted to do everything the bigger boats did.
Anyway, my opinion is to get something with a jib
and a daggerboard/cetnerboard so you can learn everything from the get-go and trailer it/launch it easily. Something that's popular so you can research online how to fix things.
I respect and understand why people are telling you to get a sunfish, but you'll feel bottle-necked after sailing it a couple times. Lazers are fun/fast but one i decent condition still runs expensive, so I would just browse craigslist and other resources, be patient and narrow it down to a few designs you like. There are a lot of GREAT deals up in the bay, I check craislists up there all the time. For $1000 OR LESS you should be able to get a reliable, clean, good sailboat with a good trailer from a good owner, and then have some money to spare for new parts and any modifications (you will immediately think about) and gear if you need it.
Lido 14's have an excellent traditional following, but in that price range make sure their flaws have been fixed(some are 40+ years old, waterlogged transoms, etc)
Coronado 15's are fast and fun, a little sensitive and wet. But usually inexpensive.
Catalina 14.2 is an overall excellent safe bet. Lots out there, jib/main, high boom, bench seating
, cuddy storage space. catalina supplies all the parts.
If you go the route of getting something really small and really simple, you will be sailing alone all the time and being bored. Then when you go to sell it, you will lose money. That's how owning a boat works. (there are rare exceptions)
I'll say it another way: If you have something with a jib, some even come with little optional spinnakers
, and you sail by next to 25' - 50' sailboats with the same kind concept of sails and controls, you'll be glad you've learned everything at once on your boat, and you're doing the same thing as them. If you have a dinky oversized windsurfboard with a mainsheet and a tiny hole for your legs to fit into while your upper body is soaking wet, you'll feel like you're failing to imitate the kind of real sailing all the real sailors get to do with bigger boats.
Buying something that seems a little complicated at first, isn't scary after using it once, nor is it like skipping a step in the learning process. You'll learn a bunch from a few hands-on sailing courses if you choose to take those, and be over the super simple dinghy
sailboats right away. If you don't take a course, for your first time sailing, go with someone who knows how to sail. It's weird what kind of misconceptions some people have, if they've never sailed on a boat before. You'll want the extra lines
and sheets and sail(s) to keep you busy and learning how it all works time after time. BTW I'm not a hater on small dinghy
boats, they're fun as hell, to a point. I just think that if you're going to drop $1000-$2000 on something to get into the sport, buy a complete set, not a stepping stone. My personal observation, is you meet people who have sailed Lido's for 40 years, and now they're in their 70s & 80's and still enjoying sailing in them -That's because they are so similar to a larger boat, but easier to maintain, and comfortable (dry) to sail for a few hours. I have yet to see a 70 year old on a lazer, crawling on hands and knees, shivering from their soaked clothes, and slouching over from having nothing to rest their back on... that's probably why I've never seen it. Everyone gets over it, and moves on to something a little bigger, with a little more to do.